Oakland

Chicago

Popular places to visit

Wrigley Field showing a city, central business district and a sporting event

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North featuring night scenes, a city and signage

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park showing a city, autumn colours and modern architecture

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Soldier Field featuring modern architecture, a city and a high-rise building

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field

Things to do

River tour boat in Chicago

Architecture River Tour

HK$381
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

HK$351
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

HK$351
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

HK$192
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

HK$328
per adult
88% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

HK$828
per adult
82% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Chicago

Top hotels in Oakland

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is HK$1,539 per night from 13 Sept to 14 Sept
HK$1,539
HK$1,807 total
13 Sept - 14 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (9,162 reviews)
"The rooms need to be refurbished.,,,bathroom not as clean as I would expect. But the hotel is over 100 yrs old."

Reviewed on 10 Sep 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is HK$1,428 per night from 22 Sept to 23 Sept
HK$1,428
HK$1,676 total
22 Sept - 23 Sept
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,894 reviews)
"From the moment we walked in, early for our reservation, we were treated like the number one priority by every staff member. The bellman #johnnyBravo #JimmyNeutron #JohnnyDanger thank you for your comic relief after a long morning of travel and for keeping our belongings safe! The room was very clean ..."

Reviewed on 10 Sep 2025

Embassy Suites by Hilton Chicago Downtown River North
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
The price is HK$822 per night from 23 Sept to 24 Sept
HK$822
HK$1,103 total
23 Sept - 24 Sept
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,295 reviews)
"Great vibes"

Reviewed on 9 Sep 2025

Freehand Chicago
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
The price is HK$1,417 per night from 22 Sept to 23 Sept
HK$1,417
HK$1,663 total
22 Sept - 23 Sept
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,767 reviews)
"N/A"

Reviewed on 10 Sep 2025

citizenM Chicago Downtown
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
The price is HK$1,185 per night from 2 Oct to 3 Oct
HK$1,185
HK$1,391 total
2 Oct - 3 Oct
includes taxes & fees
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (3,863 reviews)
"The staff was friendly and helpful."

Reviewed on 10 Sep 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is HK$1,251 per night from 22 Sept to 23 Sept
HK$1,251
HK$1,469 total
22 Sept - 23 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,829 reviews)
"This hotel is conveniently located, with close access to shopping and public transportation. Many staff members were friendly and accommodating (especially the bell hop who stored our luggage before departure). Prices were nothing special and parking access isn't great. Valet parking provided a reliable ..."

Reviewed on 9 Sep 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,427 properties in Oakland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other neighbourhoods around Oakland

Chicago Museum of Science and Industry

Hyde Park

3/5(1 area review)

Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.

Hyde Park
South Loop showing street scenes and night scenes

Near South Side

Travellers choose Near South Side for its ample dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.

Near South Side
South Loop showing a city and a skyscraper

South Loop

3/5(3 area reviews)

Soldier Field and Lake Michigan are a few top attractions in South Loop. Hop around the city on the metro at Roosevelt Station or Cermak-McCormick Place Station and check out the area's fascinating museums, panoramic lake views and popular shops.

South Loop
Chicago showing rides

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Theatre District
Default Image

Near West Side

4.5/5(14 area reviews)

Live music, theatres and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Racine Station or Polk Station (Pink Line) to get around town.

Near West Side
The Loop - Downtown which includes a river or creek

The Loop

4.5/5(187 area reviews)

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

The Loop

Oakland